Bichabd hebz and nobbebt steigeb



Patented Sept. 6, 1932 p S PATENT "OFF-ICE ON-THE-MAIN-FECHENHEM, GERMANY, .AS'SIGNORS TO GENERAL ANILINE WORKS, INC., OF NEW YORK,

in. 480,288, and in Germany .Tuly10, 1929;" In U. S. Patent N 0. 1,588,384 a manufaccreased by the aryl ture of quinone vat dyestuffs is described above formula). i which dyestuffs correspond probablytothe In the printing process, especially in printgeneral formula: I ing with not previously reduced dyestufi's a (the so-called rongalite-potash process), the reducing agent forinaldehyde sulfoxylate+ potash) is operative only during a few minutes steaming in the Mather-Flatt. this operation the reduction of the to the leuco compound aswell'a-s its on the fiber i'srto be effected, t p The above mentioned dyestuffs are so easy be reduced and show so Substituted the vegetable fiber that th drogen or a monor h )lh dmgen or haloh full yield a radical present (R in the (wherein R means an aryl group, which may or may not otherwise contain substituents, R indicates hydrogen which may be by alkyl or aralkyl, X valent substituent and gen).

a ing. s to these properties they surpass the Aicordmg F the Statements of t P known dyestuffs ofthe indigo and thioindigo fication these dyestuffs are soluble in an alkaseries usuallforvprinting' cotton line hydrosulfite solution and dye especially animal fibers various shades. I The present invention is based on the surprising observation that the above mentioned dyestufls possess such an afiinity, even to the vegetable fiber, that they can be fixed 0n the vegetable fiber, especially on cotton, accordfurthrmore a fastness' to ing t th methods of pl'intiflg usual for Vat, I the're'quirements of the practice. dyestuffs Wlth the Productlon of full and On account of their strong tinotorial inentirely fast printings. t t th 1 This fact is as more surprising as the dyeensl y By a low'economlcal stuffs, as shown by the a ove formula, are analoga of the known dimethyl-thionoline described by Bernthsen (Annalen, vol. 230,

vegetable fiber especially on cotton according I ds, navy blue to greenish blue printings distinguished by beautiful shades and a good fastness to w'ajshingand light. Some of these tile industry as to fast blue, particularly navy blue printing colours which are cheaper than the blue anthraquinone and indigoid vat dye- P This dimethyl'thionoline does stuffs hitherto used f a s ecial value are not exhibit an direct affinity to the vegetable p a fiber. It can be reduced by means of hydro- 2 of these dyestufi's g i gi F egeneral formula:- a X I s N- r 1-NHl s (wherein X means niethyl tr methoiiy).

In order: to further ill sulfite, yields however when printed on cotton in the manner usual for printing with vat dyestuffs, bluish gray rintin which are removed from the fiber by wa-sfiing.

In contradistinction thereto the dyestuffs used by the present process show an excellent aflinity to the vegetable fiber, though they contain a single carbonylic group capable of being enolized and their molecule is in- The dyestuffs yield when printed onthe ustrate ourinvention g .N. Y., A CORPORATION or. para.

Still l ddish shades are obtained I the following examples are given, the parts being by weight and all temperatures in centigrade degrees, but it is however to be understood, that our invention is not limited to the particular products nor reacting conditions mentioned therein.

E wample of a paste or 15 grs..po wder of the vat dyestufi obtained by condensin 5(-3 chlorophenylamino) -3- methyl-EZ-aminothiophenol wit chloranil are Ini-xed'w-i th' grs.

50 gm; of glycerine a V .7 V 450 grs. of a neutral starch-traganth thiekening are added, and of potassiunr'carbonate,' of the sodium salt of hanilic acid, and of a solution (111)- of vformaldehyde-sulfoxylate. V

grs.

20 grs.

grs.

'000 grs. 1 H

After having been printed and'driedfthe cotton material is steamed for-about 2-6 vininutes 1n the Mather-Flatt apparatus, well washed and after chromed'in a weakly acid to accelerate the oxidation. and soaped while'boiling hot.

bath in order Then it is rinsed In this manner abeautiful reddish'blue printis'obtai'ned. The dyestufl spends to the formula:

I e I g tures. More bluish dark'shades are obtained I using in the above example the dyestufi 'ob- A tainable by condensing chloranile with 5(3 j H chlor'o phenylar'nino) 3-1nethoXy-2-am1n0-1- 'thiophenol and corresponding to means of the dyestufi obtainablefrom 5- (fl?- methyl-phenylamino) 3 1nethyl-Q-aniinO-1- thiophenol and" chloranile, the formula:

HIQONH,

or grs. respectively-of water and Liliane thus fixed on the fiber corre- I the formula: 1

corresponding to Clear greenish blue shades are produced by the dyestufi of the formula 2 1'. Process which comprises printing vegetable fibers according to the direct printing methods usual vfor vatcyfstufis, with the qui- I p able, general for ula v.

a, was i1 ma 1m mi grou whiclilmay ormay, not otherwise contain substituents fi indicates hydrogen which maybe-substituted by alkyl or aralkyl, valent substituent and hydrogen or 2. Process which comprises printing vegetable fibers accgrdingtothe direct printing methods usual for vat dyestu nonevat dyestuffs of the probable formula:

haloa In testimony whereof we raflix our a, signa- LWILH- HECHTENBJ,

X hydrogen or a mono- Es, with the qui- 

